How This Freelance Outdoor Writer Travels and Works Remotely

Adventurer Hilary Oliver

My name is Hilary Oliver. I’m a freelance writer, editor and filmmaker. I edit the Verticulture blog for Outdoor Research, and write for places like Outside, Adventure Journal, Adventure Cyclist, Climbing. I’ve also done some short film work —- you can see the short I wrote and directed, Being Here.

I live in Denver, Colorado. I spend my spare time trail running, climbing, biking, reading, sewing, messing around with watercolors. I’d say I’m a friendly introvert. I really appreciate and need time to myself and do better one-on-one or in small groups. I get so much inspiration from things like film festivals, but they really do me in!

Adventurer Hilary Oliver

How and why did you get into adventuring/traveling?

I didn’t grow up thinking much about travel, but in college, I became more aware of what’s out there and got a mild case of the travel bug. It sounds pretty typical, but I saw photos in magazines and read books like Tales of a Female Nomad. When I finished college, I had a boatload of debt and a super low-paying job. My prospects for traveling were SUPER dim, so I actually took a job working as a janitor at a research station in Antarctica because they would cover my flight down there, and I could hold my ticket on the way back and backpack around New Zealand for a bit. Taking a trip to work someplace else was the only way I could afford to go abroad.

On my first adventure, I just packed a backpack and got on the plane. (To get the job in Antarctica I had to medically qualify, so I had to take a bunch of tests. But all I really did to prepare myself was buy some new wool socks.)

Adventurer Hilary Oliver

How do you prepare and finance your adventures?

With preparation, I usually do a combination of looking at maps, Googling, looking at Instagram hashtags and looking at guidebooks before I go someplace

Because I’m freelance, I can do most of my work remotely, as long as I have WiFi. So I actually lived in a van with my boyfriend for a year and a half (a few years ago). That way, we were able to see a lot of the western United States. But we spent most of our time sitting in coffee shops trying to meet work deadlines and/or driving to and from a trailhead or campground where we could legally spend the night in the van. That did open up a lot of adventures for us. But as we both got busier with our work, it became more difficult to be based out of a van, so we got an apartment.

I work for Outdoor Research, and they graciously keep me outfitted as far as outdoor apparel. I don’t spend a ton of money on gear —- I do try to keep things simple. And since my boyfriend and I both shoot photos for companies (a couple of our shots are in the latest Outdoor Research catalog and I was recently in an REI catalog), sometimes companies will send gear that we need so they can be featured in the magazine or catalog stories we’ll write.

Adventurer Hilary Oliver

How do you eat and sleep on the road?

I would say, not super well. 😉 When I’m on the road, I do pack a lot of snacks because I’m vegetarian and avoid dairy. That can make things difficult. So I try to pack a lot of nut butter and fruit and even veggies. I’ll sometimes pack baby food packs. But usually I eat out a lot when I’m traveling. Seeking out vegetarian spots and diners is some of my favorite parts of traveling.

When I’m backpacking, I’ll use a lightweight Big Agnes tent, like the Copper Spur, or my bivy sack from Outdoor Research. I LOVE my bivy sack. Paired with the Double Z pad from Big Agnes and my Big Agnes sleeping bag, it’s super comfy. For cooking, I’ll use either a JetBoil or an MSR Whisperlite.

If I’m just car camping, I’ll use the big ol’ Coleman stove and often sleep in the back of my Subaru with the seats folded down.

Adventurer Hilary Oliver

How do you bring your things with you?

If I’m just traveling, not going on a climbing trip, I’ll try to keep my things as pared down as possible. If I’m flying, I usually check one duffel—I love my Rangefinder Duffel from Outdoor Research—and a smaller backpack or messenger bag as my carry-on. I do not like rolling luggage—I want all my stuff to be ON my body. So, I must be able to schlep whatever I pack—if I weigh down my duffel, it’s going to be literally heavy. So I really do try to keep packing fairly minimal. (Thought that’s all relative, I know.)

I like the size of the Outdoor Research Rangefinder Duffel, and that it’s water repellent and also, it looks cool. It looks like canvas, kind of subtle, instead of bright look-at-me colors. And it’s super tough.

How do you organize things in your bags?

I definitely use smaller stuff sacks and ditty sacks within the duffel. One for outdoors clothes, one for city clothes, one for underwear. One for toiletries. Sometimes one for dirty shoes.

For me owning waterproof/water resistant bags is important. If I have to walk in the rain or miss a train and it starts snowing … I would never travel with a non-water resistant pack. Unless I’m backpacking, in which case I have a pack cover—or just throw a garbage bag in my pack just in case.

I really like my current kit—it all works really well.

Adventurer Hilary Oliver

What has been your best adventuring purchase below $100?

Within the past year, I’ve picked up two things that I really love:
The Stojo collapsible silicone travel mug, and a Bambu brand mini spork made of bamboo. When I’m flying someplace and trying to keep my carry-on light and compact, I love having a travel mug that actually folds down small instead of the big metal ones I use when I’m on a road trip. That plus my spork help me keep from using throw-away single-use cups and forks while I’m traveling. That plus my Kleen Kanteen water bottle.

What other favorite gear do you have?

As far as outdoor travel gear, two things I love and never leave home without: The Ascendant Hoody and the Aspire Jacket from Outdoor Research. The Ascendant is an active-insulation piece, which means it’s so breathable that I don’t usually have to take it on and off when I’m running or skiing. Essentially, it’s made of such a smart fabric that it functions as multiple types of layers, so I have to pack less. And the Aspire is my favorite rain jacket. It’s super tough, has nice vents and also—it comes in red, which I love.

Adventurer Hilary Oliver

What is your best advice for other adventurers?

When I first started traveling, my only jacket was from Goodwill and my plane ticket had been paid for by my employer. I didn’t know anything about gear. I just went and did it. My advice is, spend money on plane tickets not gear. If you need something but are strapped for cash, look at your local gear consignment shop. And take a look at things you ARE spending money on—could the cash from your Netflix or cable bill be going toward a trip?

I also think there’s really no wrong way to have an adventure—simply because that’s what a real adventure is, right? We all learn things the hard way sometimes—like, when we’re cold and wet. Or, things just don’t turn out the way we thought they would. But, barring life-threatening situations, that’s usually how we make a memory!

My boyfriend and I took a trip last year to Ireland in the winter. We rented a camper van and drove around the south and west coast, which is something I’d NEVER recommend to anyone. The campgrounds were closed because it was winter, the van was too big to park in any cities. We would have been better off in a rental car, staying at Bed and Breakfasts. But we had gone by the seat of our pants. And we had fun. I’ll never forget the night we spent in the van out on the pier in Doolin, just getting rocked by the wind in a storm. We could hear the boulders rolling in the ocean below. It was so cold and there was no place else we could stay. No, we wouldn’t necessarily have planned it that way—but it definitely made a memory and I’m grateful for it.

Adventurer Hilary Oliver
Photo credit: Brendan

What will the future bring?

We’re looking at doing self-supported bike packing trip on the White Rim trail in Canyonlands National Park over Thanksgiving. I love traveling by bike, and the Utah desert is so fabulous in November. I can’t wait!

Follow Hilary Oliver on her website, Instagram, Twitter


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